Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions
Year: 2020
Type: article
Abstract: K3Fe(CN)6 and NaIO4 serve as catalytic co-oxidants for osmium-catalyzed dihydroxylations that are performed under near-neutral conditions with K2S2O8 as the stoichiometric oxidant and Na2HPO4 as the base.By using either quinuclidine or hydroquinidine 1,4-phthalazinediyl ether [(DHQD)2Phal], good yields of racemic or enantioenriched diols are obtained.This simple, biphasic procedure offers advantages over other neutral dihydroxylation protocols that use N-methylmorpholine oxide as the stoichiometric oxidant, by suppressing the secondary catalytic cycle that leads to reduced enantioselectivities.The utility of the procedure, which is nicely suited for base-labile starting materials or products, is demonstrated by performing the dihydroxylation in the presence of an aliphatic aldehyde moiety.
Source: ARKIVOC
Authors: Shawn Blumberg, Stephen F. Martin
Institution: The University of Texas at Austin
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
Funder: Welch Foundation
Award: G6867265530
OpenAlex ID: W3045016301